1-Hydroxybenzotriazole → tert-butyl (1S)-1-{[methoxy(methyl)amino]carbonyl}pentylcarbamate

HRID 342128Notes

Reaction equation

HRID 342128 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][CH2:15][CH3:16])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:18][NH:19][O:20][CH3:21].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>>[CH3:21][O:20][N:19]([CH3:18])[C:10](=[O:12])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733747N-tert-Butoxycarbonyl-L-norleucine

Product 1

HCID 10061913tert-butyl (1S)-1-{[methoxy(methyl)amino]carbonyl}pentylcarbamate

Procedure

2(S)-(tert-Butoxycarbonylamino)hexanoic acid (24.6 g, 0.106 mol), N,O-dimethylhydroxylamine hydrochloride (15.5 g, 0.15 mol), EDC hydrochloride (22.3 g, 0.117 mol) and HOBT (14.3 g, 0.106 mol) were stirred in dry, degassed DMF (300 mL) at 20° C. under nitrogen. N-Methylmorpholine was added to obtain pH 7. The reaction was stirred overnight, the DMF distilled under high vacuum, and the residue partitioned between ethyl acetate and 2% potassium hydrogen sulfate. The organic phase was washed with saturated sodium bicarbonate, water, and saturated brine, and dried with magnesium sulfate. The solvent was removed in vacuo to give the title compound.

Workup

  1. customin dry
  2. customdegassed DMF (300 mL) at 20° C. under nitrogen
  3. additionN-Methylmorpholine was added
  4. customto obtain pH 7
  5. distillationthe DMF distilled under high vacuum
  6. customthe residue partitioned between ethyl acetate and 2% potassium hydrogen sulfate
  7. washThe organic phase was washed with saturated sodium bicarbonate, water, and saturated brine
  8. dry with materialdried with magnesium sulfate
  9. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-979864d0318e4cc1a360a80edefdafa7
Source dataset
uspto-grants-1999_01
Patent number
US05856326

Reaction notes

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